Organocatalytic Enantioselective Mannich-Type Reaction of Phosphorus Ylides:  Synthesis of Chiral N-Boc-β-Amino-α-methylene Carboxylic Esters

The first asymmetric Mannich-type reaction of stabilized phosphorus ylides and N-Boc aldimines was described promoted by a readily available and recyclable chiral bisthiourea organocatalyst. Subsequent reaction with formalin smoothly provides N-Boc-β-amino-α-methylene carboxylic esters in a highly e...

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Published in:Journal of the American Chemical Society 2008-02, Vol.130 (8), p.2456-2457
Main Authors: Zhang, Yan, Liu, Yan-Kai, Kang, Tai-Ran, Hu, Ze-Kai, Chen, Ying-Chun
Format: Article
Language:English
Subjects:
Carboxylic Acids - chemical synthesis
Carboxylic Acids - chemistry
Catalysis
Esters - chemical synthesis
Esters - chemistry
Molecular Structure
Phosphines - chemistry
Stereoisomerism
Thiourea - analogs & derivatives
Thiourea - chemistry
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cited_by cdi_FETCH-LOGICAL-a351t-ad14edefe374a1234f563ca9e6aac76a98fcbac38312d062a0d947dbd65d787f3
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container_issue 8
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container_title Journal of the American Chemical Society
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creator Zhang, Yan
Liu, Yan-Kai
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description The first asymmetric Mannich-type reaction of stabilized phosphorus ylides and N-Boc aldimines was described promoted by a readily available and recyclable chiral bisthiourea organocatalyst. Subsequent reaction with formalin smoothly provides N-Boc-β-amino-α-methylene carboxylic esters in a highly enantiomerically enriched form (up to 96% ee).
doi_str_mv 10.1021/ja7114844
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Carboxylic Acids - chemical synthesis
Carboxylic Acids - chemistry
Catalysis
Esters - chemical synthesis
Esters - chemistry
Molecular Structure
Phosphines - chemistry
Stereoisomerism
Thiourea - analogs & derivatives
Thiourea - chemistry
title Organocatalytic Enantioselective Mannich-Type Reaction of Phosphorus Ylides:  Synthesis of Chiral N-Boc-β-Amino-α-methylene Carboxylic Esters
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